Furthermore we showed that resistant virus to imidazo 1, 2 apyrrolo3,2c pyridine analogue 10a ag110 is crossresistant with three other inhibitors of pestivirus replication i. Phosphinefree palladiumcatalyzed direct arylation of 2 phenyl imidazo 1, 2 a pyridine has been developed with the concept of using silveri carboxylate. Preparation of the imidazo 1, 2 a pyridines c5nucleosides. Phosphinefree palladiumcatalyzed direct c3 arylation of 2. Synthesis of novel imidazo1,2apyridines and evaluation of. Synthesis of imidazo1,2apyridine derivatives and their. The imidazo 1, 2 a pyridines are found to possess various potential biological activities. Molecular modeling was used to identify biophoric structural patterns that are common to 16 compounds. Page 273 synthesis of new 6halogenoimidazo1,2apyridines by srn1 reactions maxime d. Synthesis and antiviral activity of imidazo1,2apyridines. Imidazopyridines and imidazopyrimidines have been prepared and tested for their antibacterial activity in vitro. An efficient synthesis of new imidazo1,2 a pyridine6. Different routes for accessing the desired compounds were examined and a few specially designedsubstrates have been utilized further to afford the.
From the synthesized compounds, 4, 15, and 21 were highly active against human cytomegalovirus with a therapeutic index superior to 150. Nov 19, 2015 gueiffier a, mavel s, lhassani m, elhakmaoui a, snoeck r, andrei g, chavignon o, teulade jc, witvrouw m, balzarini j 1998 synthesis of imidazo 1, 2a pyridines as antiviral agents. The synthesis and antiviral activity of original dibromoimidazo 1, 2 a pyridines bearing a thioether side chain are reported. Synthesis and antimicrobial screening of mannich bases of imidazo1,2a pyridine, 16, 396, 2003 douhal a. Green synthesis of imidazo1,2apyridines using calix6. The synthesis of 5,6,7,8tetrahydroimidazo1,2apyrimidinehydrazone derivatives 8ak described in this paper were prepared according to the synthetic scheme 1. The synthesis of original imidazo 1, 2 a pyridines bearing a thioether side chain at the 3 position and their antiviral activity are reported. Dec 19, 2018 tuberculosis is an airborne disease, mostly affecting young adults in their productive years. Synthesis of new 6halogenoimidazo1,2apyridines by srn1.
By the reaction of 2benzoylmethylimidazoles 1a, b with polarized olefins 2, 3 in the presence of k2co3, the corresponding imidazo1,2apyridine derivatives 4, 5 were obtained. This methodology, developed for the synthesis of 3aroylimidazopyridines, involves a copperii acetatecatalyzed aerobic oxidative amination and. Green synthesis of imidazo1,2apyridines in aqueous medium. It was coupled with a variety of aryl alcohols in one pot to obtain a series of imidazo1,2pyridine derivatives possessing aryl ether moiety at c3 position. Synthesis of acyclocnucleosides in the imidazo1,2a. A large number of substituted imidazo 1, 2 a pyridines have been synthesized and tested for various biological activities such as antiulcer 1, antibacterial 2, antimicrobial 3, antifungal 4, and antiviral 5 6 agents. Due to the importance of environmentally compatible solvent in multicomponent reactions, herein we report an efficient and sustainable catalystfree synthesis of imidazo 1,2a pyridines via groebke. Compounds 3al were prepared from reaction between different substituted 2bromo1arylethanones 2al. For the imidazo 1, 2 a pyridines with various substituents on benzene or pyridine ring and a variety of azoles, the reaction proceeded smoothly to give the 3azol 2 yl imidazo 1, 2 a pyridines in. Thus, derivatives of 2amino3aroyl imidazo l,2apyridines have been evaluated as antiviral agents. The required building block of imidazopyridine was synthesized from commercially available 5,5diaminopyridine3ol followed by four step sequence. Here we report the synthesis and antiviral activity of 3dithiolan, oxathiolan and dithiolan2ylimidazo1,2apyridines bearing a 7 or a 8methyl.
Imidazo1,2apyridine scaffold as prospective therapeutic. Novel 2 or 3aryl substituted imidazo1,2apyridines and their synthesis are described. Synthesis and antiviral activity of an imidazo1,2a. This transformation provides a rapid and concise access to multifunctional imidazo1,5apyridines.
Synthesis of imidazo1,2 a pyridines organic chemistry portal. Results and discussion herein we describe the synthesis of 3a and 3b scheme 1 starting respectively from the commercially available 2amino5chloropyridine 1a or 2amino5bromopyridine 1b by condensation with 1,3. General description in vivo antitrypanosomal activity of imidazo1,2apyridiness in the stib900 mouse model has been investigated packaging 5, 25 g in glass bottle. In conclusion, we have demonstrated that the synthesis of 2phenylimidazo1,2. Synthesis of acyclocnucleosides in the imidazo 1, 2 a pyridine and pyrimidine series as antiviral agents. Jan 30, 2019 imidazo 1, 2 a pyridines are probably the most common nitrogenbridgehead fused heterocycles used in pharmacology research, attributed to their activities spanning a diverse range of targets. A large number of substituted imidazo1,2apyridines have been synthesized and tested for various biological activities such as antiulcer 1, antibacterial 2, antimicrobial 3, antifungal 4, and antiviral 5 6 agents. Polycyclic imidazo1,2apyridine analogs synthesis via.
Synthesis and antimicrobial screening of novel series of. Synthesis and antiviral activities of 3aralkylthiomethylimidazo1,2. For the imidazo1,2apyridines with various substituents on benzene or pyridine ring and a variety of azoles, the reaction proceeded smoothly to give the 3azol2ylimidazo1,2apyridines in. Here, ligandbased drug design approach yielded a series of 23 novel 64nitrophenoxy1himidazo4,5bpyridine derivatives. One of the most common strategies uses 2aminopyridine or 2aminopyrimidine, and. In several drug formulations imidazo 1, 2 a pyridines are widely used. The synthesis and the antiviral activities of c3 acyclic nucleoside analogues of imidazo1,2apyridine and pyrimidine are reported. This catalyst system is recoverable with a simple extraction using an organic. Jul 26, 2019 synthesis and antiviral activity of novel erythrofuranosyl imidazo 1, 2 a pyridine cnucleosides constructed via palladium coupling of iodoimidazo 1, 2 a pyridines and dihydrofuran. We demonstrated earlier that the imidazo 1, 2 apyrrolo3,2c pyridines 1a, b selective inhibit the replication of pestiviruses by targeting a region of the finger domain of the rdrp. This catalyst system is recoverable with a simple extraction using an organic solvent. In previous papers, we reported the synthesis and biological activity of a series of imidazo 1, 2 a pyridines as antibacterials and antifungals. A simple and economic way of synthesis of imidazo1,2apyridines using 2aminopyridine and phenacylbromide derivatives in aqueous medium by microwave irradiation has resulted in bridged azaheterocycles in good to excellent yields. A series of 3substituted imidazo1,2apyridines wa synthesized as potential antiviral agents.
Apr 10, 2001 structure and absolutestereochemistry of compound 78 was determined by xray crystallography. Imidazo1,2apyridine is one of the most potential bicyclic 56 heterocyclic rings that is recognized as a drug prejudice scaffold due to its broad range of applications in medicinal chemistry such as anticancer, antimycobacterial, antileishmanial, anticonvulsant, antimicrobial, antiviral, antidiabetic, proton pump inhibitor, insecticidal activities. Synthesis of imidazo1,2a pyridines as antiviral agents. Phosphinefree palladiumcatalyzed direct arylation of 2phenylimidazo1,2 a pyridine has been developed with the concept of using silveri carboxylate.
Hydrazone derivatives are known to exhibit a wide variety of biological activities including antimicrobial. Crozet, caroline castera, mustapha kaafarani, michel p. A short and practical arylation of imidazo1,2apyridine and imidazole derivatives with aryl halides or aryl boronic acids as coupling partners was successfully carried out using phosphinefree siprpdallylcl as the catalyst sipr. Examples of bioactive agents possessing imidazo1,2apyridine cor. Imidazo 1, 2 a pyridines c5nucleosides may be prepared fromimidazo 1, 2 a pyridines by condensation of a lithiatedimidazo 1, 2 a pyridine with a lactone in a method analogous to that. It has long been known that imidazo1,2apyridine derivatives exhibit diverse biological activities 1 and were used as antiviral, 2 antiulcer, 3 antibacterial, 4 antifungal, 5 antiprotozoal, 6 antiherpes, 7 antiinflammatory.
Imidazo1,2apyridine scaffold as prospective therapeutic agents. S1 supporting information a practical twostep synthesis of imidazo1,2apyridines from nprop2yn1ylpyridin2amines david sucunza,a abdelouahid samadi,a mourad chioua,a daniel b. Synthesis of this moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry. However, imidazo4,5bpyridines and imidazo4,5cpyridines, despite the similar activity, exhaustive and target based research on development of many compounds as antitumor, antimicrobial, antiinflammatory, antiviral, immunomodulatory, antidiabetic modulators have not made their way to the market and clinic. The synthesis of original imidazo1,2apyridines bearing a thioether side chain at the 3 position and their antiviral activity are reported. Synthesis of nheterocycles benzofused nheterocycles synthesis of imidazo1,2apyridinesrecent literature. The synthesis and the antiviral activities of c3 acyclic nucleoside analogues of imidazo 1, 2 a pyridine and pyrimidine are reported.
Crystal correlation of heterocyclic imidazo1,2 a pyridine. Structure activity relationship studies indicate sar that a modulation of. The intensely increasing multidrug resistant microbial infections have encouraged the search for new antimicrobial agents. Onepot synthesis of tetracyclic fused imidazo 1, 2 a pyridines via a threecomponent reaction a novel threecomponent reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo 1, 2 a pyridines in a onepot fashion utilizing readily available 2 aminopyridines, isatins and isocyanides.
The cyclo condensation reactions of 1,1,3trichloro acetone with 2aminopyrimidine 1 to 2dichloromethylimidazo1,2apyrimidine 2 was carried out in ethanol at reflux temperature for. The reaction also enables the formation of alkenylsubstituted. Synthesis of imidazo1,2 apyridine derivatives as antiviral agents article in arzneimittelforschung 514. Synthesis of imidazo 1, 2 a pyridine derivatives as antiviral agents. However, the existing synthetic methods have drawbacks such as relatively high reaction temperatures, long reaction times and the difficult posttreatment. Its synthetic method started from the reaction of 2aminopyridines with acetophenones. Imidazopyridines are considered as important class of fused heterocyclic compounds possessing interesting biological and pharmacological properties as antiviral, 5 antifungal, 1 anti varicellazoster, 2 antibacterial 4 and anticancer agents. Synthesis of imidazo1,2apyridine derivatives as antiviral agents. Whereas the preparation of 2 or 3arylimidazo1,2apyridines has received considerable attention,5 modi. Synthesis of imidazo1,2apyridines as antiviral agents. Using of calixnarenes in water provided a hydrophobic cavity that successfully carried out the synthesis reactions at short times with high yields.
Preparation of imidazo1,2anheterocyclic derivatives. Imidazo 1, 2 a pyridines have received a significant attention in pharmaceutical industry owing to their interesting biological activities including antibacterial 1,antifungal 2, antiviral 35 and anti. A series of imidazo 1, 2 a pyrrolo 2,3c pyridines has been prepared and evaluated for their antibvdv activities in mdbk cells. Methylsulfinylimidazopyridine derivative 7 obtained by the reaction of 5b with mchloroperbenzoic acid mcpba, easily underwent nucleophilic substitution to. Chemistry ethyl imidazo1,2apyridine2carboxylate hydrobromide 2 was obtained from 2aminopyridine and ethylbromopyruvate by a 2step procedure. From the synthesized analogues bearing modifications of the substituents at positions 2, 3, 7 and 8, compounds 10a, b, 16, 24, 25 and 26 exhibited significant antibvdv activities. Imidazo1,2apyridines are useful building blocks for a number of biologically and pharmaceutically valuable compounds. This invention pertains to imidazo1,2apyridine cnucleosides, morespecifically, imidazo1,2apyridine c3nucleosides andimidazo1,2apyridine c5nucleosides, which have antiviral activity andlow toxicity a nd which offer improved metabolic stability, and therefore,longer halflives in vivo. This protocol efficiently catalyzes the ch arylation of 2 phenyl imidazo 1, 2 a pyridine with aryl iodides to afford the corresponding 2 phenyl3aryl imidazo 1, 2 a pyridines in moderate togood yields. Synthesis of imidazo1,5 a pyridines organic chemistry portal. Direct arylation and suzukimiyaura coupling of imidazo1. The reaction also enables the formation of alkenylsubstituted imidazoheterocycles by using unsaturated ketones as substrates.
Compounds 3al were prepared from reaction between different. The compounds have local anesthetic properties and are useful as local anesthetic agents, calcium channel blocking agents and antisecretory agents. Deep eutectic solvents are becoming more popular nowadays since they are green, safe and often save raw materials and energy compared to organic solvent. Phosphinefree palladiumcatalyzed direct c3 arylation of.
Imidazo1,2pyridinebased tosylhydrazone was prepared and treated with k 2 co 3 in dioxane at 110c to generate the corresponding carbene in situ. Preparation of imidazo1,2anheterocyclic derivatives with. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. The 6chloroimidazo1,2bpyridazine 1a was synthesized by condensation of. A structureactivity relationship study of the affinity of selected imidazo 1, 2 a pyridine derivatives, congeners of zolpidem, for the omega 1 subtype of the benzodiazepine receptor. General description in vivo antitrypanosomal activity of imidazo 1, 2 a pyridiness in the stib900 mouse model has been investigated packaging 5, 25 g in glass bottle. The synthesis and antiviral activity of original dibromoimidazo1,2apyridines bearing a thioether side chain are reported. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of cc bond and cn bond of ethyl group with molecular oxygen as terminal oxidant in. A novel threecomponent reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo1,2apyridines in a onepot fashion utilizing readily available 2aminopyridines, isatins and isocyanides. Synthesis of novel imidazo1,2apyridines and evaluation. Synthesis and antiviral activity of 3substituted imidazo 1, 2a. As a part of our studies on nitrogen bridgehead heterocycles, we have recently reported the synthesis and the antiviral activity of 7 and 8methyl3benzylthiomethylimidazo1,2apyridine as a member of a new class of anticmv agents.
Us4382938a imidazo1,2a pyridine derivatives and their. An efficient synthesis of imidazo1,2apyridines naresuan. In an attempt to find new bioactive molecules, a series of mannich bases n,ndimethyl17methyl2arylimidazo1,2apyridin3ylmethanamines 4al were synthesized by mannich reaction of 7methyl2arylimidazo1,2apyridines 3al with paraformaldehyde and n,ndimethyl amine. A cuicatalyzed aerobic oxidative synthesis of imidazo1,2 apyridines from 2aminopyridines and acetophenones is compatible with a broad range of functional groups. Tuberculosis is an airborne disease, mostly affecting young adults in their productive years.
Herein, we report the synthesis of imidazo1,2apyridines, imidazo1,2apyrimidines, and imidazopyridazines with fluorinated side chains following an efficient strategy developed by hajra et al. Pharmacological potential and synthetic approaches of. Imidazo1,2apyridine synthesis organic chemistry portal. Here, ligandbased drug design approach yielded a series of 23 novel 64nitrophenoxy1h imidazo 4,5bpyridine derivatives. A highly efficient synthesis of 3formyl imidazo 1, 2 a pyridine and imidazo 1, 2 apyrimidine, under cucatalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. Herein, we report the synthesis of imidazo 1, 2 a pyridines, imidazo 1, 2 a pyrimidines, and imidazopyridazines with fluorinated side chains following an efficient strategy developed by hajra et al.
Synthesis and evaluation of antituberculosis activity of. Here we report the synthesis and antiviral activity of 3dithiolan, oxathiolan and dithiolan 2 yl imidazo 1, 2 a pyridines bearing a 7 or a 8methyl group and a thioacetal compound as ring opening derivative. Synthesis of imidazo1,2apyridine derivatives has been the subject of. Synthesis of imidazo 1, 2apyridine derivatives as antiviral agents article in arzneimittelforschung 514. Here we report the synthesis and antiviral activity of 3dithiolan, oxathiolan and dithiolan2yl imidazo 1, 2 a pyridines bearing a 7 or a 8methyl group and. Synthesis of imidazo1,2apyridine derivatives as antiviral. Synthesis and antimicrobial screening of chalcones. In recent years, new preparative methods for the synthesis of. Synthesis and antiviral activity of an imidazo1,2apyrrolo. Imidazo1,2apyridines are probably the most common nitrogenbridgehead fused heterocycles used in pharmacology research, attributed to their activities spanning a diverse range of targets.
Copperi catalysis enables a direct transannulation of nheteroaryl aldehydes or ketones with alkylamines via c sp 3h amination in the presence of oxygen as the sole oxidant. In several drug formulations imidazo1,2apyridines are. As a part of our studies on nitrogen bridgehead heterocycles, we have recently reported the synthesis and the antiviral activity of 7 and 8methyl3benzylthiomethylimidazo 1, 2 a pyridine as a member of a new class of anticmv agents. Structureactivity relationship sar studies identified hydrophobicity logp as the most important factor for activity. Imidazo1,2apyridine cnucleosides as antiviral agents. Cucatalyzed synthesis of 3formyl imidazo1,2apyridines. Direct arylation and suzukimiyaura coupling of imidazo1,2a. Synthesis of imidazo 1, 2a pyridines as antiviral agents. Supporting information a practical twostep synthesis of. Moreover, the synthesis of the imidazo1,2apyridine and imidazo1,2apyrimidine ring systems has been widely investigated 2331. In this research, green synthesis of imidazo 1, 2 a pyridines in the presence of calixnarenesso 3 h as a bronsted acid catalyst and surfactant is described. In heterocyclic moiety, imidazo 1, 2 a pyrimidines are the subject of immense interest for their antimicrobial activity and also for their analgesic, antipyretic. A revised approach to the synthesis of 3acyl imidazo1,2. N,nbis2,6diisopropylphenyl4,5dihydroimidazol2ylidene siprpdallylcl complex.
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